Process of making acetyl-salicyl-phenetidin.



UNITED STATES Patented December 27, 1904.

PATENT OFFICE.

PROCESS OF MAKING ACETYLFSALICYLPHENETIDIN- SPECIFICATION forming partof Letters Patent No. 778,556, dated. December 27, 1904.

Application filed April 11, 1904. Serial No. 202,635.

1'0 (all III/tom, it may concern.-

Be it known that I, SAMUEL LEWIS SUMMERS, a citizen of the UnitedStates, residing in the city of Philadelphia, State of Pennsylvania,have invented certain new and useful Improvements in Processes ofProducing Acetyl-Salicyl-Phen etidin,of which the following is a full,clear, and exact description.

My invention relates to a new process for producingacetyl-salicyl-phenetidin, a chemical product invented by me anddescribed in Letters Patent No. 706,356 granted to me, dated August 4,1902. The said product is the crystalline derivative having the chemicalformula ()nHnNOr, resulting from the reaction of acetic acid andsalicylic acid on phenetidin as the base. In said patent I described andclaimed a process of producing it, which consisted in preparing asalicyl-phenetidin compound and then acetylizing this by means of aceticanhydrid.

My present and newly-invented process consists, speakinggenerally. inpreparing a compound of acetic acid and salicylic acid and using this asan acetylizing agent, so to speak, causing it to react onpara-amido-phenetol, the resultant crystals being then purified bywashing or recrystallizing from ethylic alcohol, chloroform, or othersuitable solvent.

In carrying out my new process practically I first make a pureacetyl-salicylic-acid compound from one hundred and two parts, byweight, of anhydrous acetic acid and one hundred and thirty-eight parts,by weight, of salicylic acid. Of this compound I take one molecule orone hundred and eighty parts, by weight, and combine it with one hundredand thirty-seven parts, by weight, of para-phenetidin, adding justenough xylene to dissolve the mixture when heated to its boiling-point.

The resultant solution desired is then obtained by heating the mass inan autoclave to a temperature of about 150 centigrade for a period ofabout six hours. It is then allowed to cool, and the desired crystallinederivative is then separated from the condensation which takes place bywashing or recrystallizing from ethylic alcohol, chloroform, or othersuitable volatile solvent. The resultant crystals have the chemicalformula CnHnNOi, are pure white, tasteless, and form in needle-likestructures, rather than in plates, as do many phenetidin compounds, andare completely soluble in alcohol, ether, benzin, and chloroform. Theproduct does not differ substantially from the product described in mysaid former patent; but my new process hereinabove described forproducing it has the advantages of simplicity and economy, is moredirect, and productive of greater certainty in the results sought for.

Having thus described my invention, what I claim as new, and desire tosecure by Letters Patent, is

The process described for producing acetylsalicyl-phenetidin, whichconsists in causing an acetyl-salicylic-acid compound to react onpara-phenetidin, in the presence of xylene as a solvent; heating theadmixture until it dissolves, then allowing it to cool and separatingthe resultant formed crystals from the liquor of condensation, andfinally purifying the resultant crystalline product; substantially asdescribed.

In testimony whereof I have hereunto affixed my signature this 5th dayof April, A. D.

SAMUEL LEWIS SUMMERS. Witnesses:

B. F. TAPPAN, MAE F. NAHILL.

